THE SCENE in Dale Earnhardt Jr.'s second-floor office at JR Motorsports in Mooresville, N.C., last Thursday afternoon was somber. An hour earlier Junior had announced that at season's end he will leave Dale Earnhardt Inc., the only team he has driven for in his eight-year Nextel Cup career. His eyes dewey from the emotion of the day, Earnhardt welcomed a reporter, and before the interview began, he asked a question of his own: "Man, am I doing the right thing?"

On the surface it seemed a no-brainer. The 32-year-old will be the most coveted free agent in NASCAR's 59-year history. He brings an impressive résumé (17 wins and four top 10 points finishes), the sport's largest and most rabid fan base and a sponsor, Budweiser, willing to shell out $20 million a year.

But to gain his freedom, Earnhardt had to walk away from DEI, the organization his father, Dale Sr., founded with the hope that his son would one day take over. It was the hardest decision Junior ever made—and difficult for his entire family. As Dale Sr.'s sister Kathy Earnhardt sat in the front row of Junior's press conference, she wept. "When something like this happens, it's a reminder that Dale isn't around," she said later, her tears still falling. "If he was here, none of this would have happened."

The story of why Earnhardt left is rooted in his fractured relationship with his stepmother, Teresa Earnhardt. In 1981, when Dale was six, he and his sister Kelley, who was eight, were sent to live with their father after a fire destroyed their mother Brenda's house. (She and Dale Sr. divorced in 1978.) Dale Sr. and Teresa (who became Earnhardt's third wife, in 1982) were often on the road, and the kids were left with nannies and relatives. Junior's relationship with Teresa grew frostier during his preteen years. Little E raised hell in those days—he got kicked out of a private school for fighting—and Junior says it was largely Teresa's call to send him to military school: "Sure as hell wasn't my decision. It wasn't fun, I'll tell you that."

Dale Sr. named Teresa co-owner of DEI in 1996, and she played a hands-on role in expanding what had been his hobby into a three-car, multimillion-dollar colossus with 400 employees. Junior came aboard as a driver in 1998, first in the Busch Series and then in a full-time Cup ride two years later. Business was thriving, but when Dale Sr. died on the last lap of the 2001 Daytona 500, the one thread that bound Teresa and Dale Jr. unraveled. Without her husband around, the reticent Teresa rarely came to the track. (Driver Kevin Harvick once called her a "deadbeat owner.") She and Junior seldom spoke or appeared together, and it seemed that Teresa (who refused SI's request for an interview) still considered Little E to be a reckless apple-cheeked kid. Last December, in a rare public statement, she told The Wall Street Journal that Junior "has to decide if he wants to be a driver or a celebrity." And Junior's feelings about her haven't changed since he and his sister moved into their father's house. "Me and Teresa do not see eye to eye," he says. "I wish we did, but we don't."

The feud boiled over as Junior tried to negotiate an extension of his contract with DEI, which expires at the end of the season. Earnhardt, who was represented by Kelley in the negotiations, felt ready to assume majority ownership of DEI and control of its day-to-day operations—two things that Dale Sr. told SI, in one of his last interviews, that he wanted his son to have. Junior wanted control so he could loosen the purse strings and spend more on R&D; Earnhardt has won only twice since the start of the 2004 season, a slump most in the garage attribute to inferior equipment. Sources at DEI say Teresa offered Junior what he wanted; a source close to Junior said the offer included 51% ownership but not day-to-day control. After playing a crucial role in building DEI, Teresa couldn't bring herself to turn it over—even though, without its marquee driver, DEI will struggle to remain competitive.

And so last Thursday—three days before Mother's Day—Earnhardt announced he was on the market. Several owners have already declared their desire to sign him, and those who haven't are just being coy. The deciding factor could be a team's ability to provide Earnhardt with something he couldn't find at DEI: the feeling that he is part of a family. "Man, I look at the fun that other drivers have with their owners," Earnhardt said last Thursday. "I want a guy who's going to be at the track and give me feedback. I want to feel really part of an entire organization. That's a big part of racing, and I want that."

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